New label Penumbra, the brainchild of formers fashion editors Courtney Bennett and Stephanie Giorgio, is tackling the challenges of effortless, day to night style. "[Penumbra] really came about when we were both trying to find simple, unadorned clothing to enhance our accessories. We love the idea of traveling easy as well as going from day to night," Bennett told us, and their cowl back maxi dress ($262) does just that! "It is such a versatile style," says Bennett. "I have worn it to the beach over a bathing suit and to a wedding!" It comes in three neutral colors—gray, black and navy—and drapes perfectly over the hips for a style that is flattering on every body type. Wear it with bold bangles and platforms for a dressy look or show off its simplicity with casual flats and a slouchy bag. Shop all the versatile styles at singer22.com.